


Pretty in Pink

by Mesmeret



Category: Supernatural
Genre: Anal Sex, Blow Jobs, Blow job under a dress, Cas wears glasses, Crossdressing, Crossdressing Dean, Crossdressing Kink, Dancing, Deepthroating, Dirty Talk, Dominant/Top Dean, Love Confessions, M/M, Oral Sex, Rimming, Submissive/Bottom Castiel, like whoa Dean has a filthy mouth
Language: English
Status: Completed
Published: 2013-08-14
Updated: 2013-08-14
Packaged: 2017-12-23 11:06:28
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,712
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/925640
Author URL: https://archiveofourown.org/users/Mesmeret/pseuds/Mesmeret
Summary: <blockquote class="userstuff">
              <p>Dean and Castiel have been dating since meeting at the Queens of the Stone Age concert. Castiel is enamored by his dress wearing lover but doesn't want to scare the man who's 5 years his younger. But after a fun night of swing dancing, Dean confronts him about it. Things are much better now they know they love each other. Then Castiel expresses it by deep throating Dean and Dean fucks Castiel.<br/>Yeah.<br/>A sequel to <a href="http://archiveofourown.org/works/902534">Quick and to the Pointless</a></p><p>---------------------<br/>Sorry, not sorry for this signal boost, but please check out my <a href="https://docs.google.com/forms/d/1G1Z_a9Rx2R3ixl5sKpO6bj8lLAnxSv5P6m0PvZEE7N8/viewform"> Watch Me Write</a> if you're interested in participating in the action!</p>
            </blockquote>





	Pretty in Pink

****

Dean got out of his Impala looking at the small yellow house with the address number on the blue front door. After double checking that it matched the number on Castiel's business card, Dean walked up the steps with a duffel bag. Before he rang the doorbell, Cas opened up the door looking like he just time traveled from a party in the 50s. His hair slicked back and was wearing tailored jeans below a white undershirt. Dean sucked in a breath and blushed deeply.

"Hey, Cas. You look hot."

The older man gave him a small smile before ushering him inside the house. Dean was impressed by how organized and clean everything was. Castiel always gave off a sense of absentmindedness and so Dean was preparing himself for book clutter. Instead, there were walls of bookshelves with books surrounding simple but comfortable looking furniture. Castiel led him to the bathroom, "You can get changed here. I'll finish up in my room. I can't wait to see you."

Both of them blushed before Dean shut the door. He pulled out a soft pink dress with red lining as well as proper undergarments. He nervously undressed. Castiel was so supportive of Dean's crossdressing. He just wished the world was too.

First was the underwear, a pair of soft pink panties that he got at the mall. Then he put on the matching B cup bra with the fake boob inserts. He couldn't help placing his hands over his tits and check himself out in the mirror. He looked hot. Finally, he put on the dress. He looked fuckable already. Doing a few shakes of his hips, he enjoyed the movement of the knee length skirt brushing against his shaved legs.

Looking at his face, he debated putting on makeup. He was afraid he would look like a painted whore, but then again his face definitely looked a little too masculine without it. He looked through the make-up palette he bought at the same shop in the mall. He tried to remember what the Vogue Magazine article stated for a "Fun Summery Look", so Dean grabbed the little applicator brush and dabbed it into the pale bronze before going over his eyelids with it. This was the first time he had ever got to apply eye shadow on himself. His hand was trembling but it looked good so far. He remembered a passage that talked about bringing out your eye color. So he went for the moss green to line his lids. He was stunned. His eyes looked amazing. Now he had to do mascara. Looking at the applicator, he prayed he wouldn't poke his eye out with the bristled terror.

Thankfully, he only smudged his cheeks with the inky black. After wiping it off with some toilet paper and water, he put on some pink blush and cherry red lipstick. He worried his hair a bit. It had grown out enough to look like Winona Ryder's hair. He looked at the remaining items in the bag--a dark pink headband and black patent leather Mary Janes with small heels. With a shy smile, he pulled them out and placed the makeup and his other clothes into the bag. He got out of the bathroom and looked around to see Cas smoking on a pipe looking at him with Buddy Holly glasses. Dean bit his lip trying to suppress a moan.

Cas couldn't believe the sight before him. Dean looked gorgeous and comfortable with himself. Whenever they would hang out for coffee, Dean would sit up rigid and stiff. But the moment the guy was wearing something light and cute, he would not have those barriers or hold ups. Plus, Dean looked superb in dresses and skirts. Cas set down his pipe and motioned to Dean to come over. Dean walked over with a shy smile, "Am I pretty?"

"Yes, yes you are, beautiful," Castiel pulled him close and nuzzled the tone abdomen of his lover. "I think you're gonna make some people jealous."

Dean blushed and caressed Castiel's ears being mindful on not ruining that perfect hair. "Thank you, Babe. When do we have to leave?"

"Well, did you eat supper yet?"

"No," Dean whispered softly. It was only 6:30.

"Okay, I have something in the fridge or we could go out."

"Um, could we eat here?" Dean raised a brow.

"Of course," Castiel stood up from his chair and headed into the kitchen. "I've got the makings for um, well... Sandwiches?"

Dean laughed and walked over to see just how bad Cas' refrigerator was. Looking over the sweater vested shoulder, Dean saw some condiments, cheddar cheese that was unopened, and some ham. "How about a picnic in the living room?"

"I love how you always live life on the edge."

Dean savored the yelp the older man gave when he slapped Castiel on the ass. "Damn right I do."

They went on to make some sandwiches while talking about the night's concert. Dean was excited to dance to some jovial swing music while Cas was looking forward to listening to the old trumpet players rift with each other. Once they were settled in the living room with Cas' record player playing some Fats Waller, they ate their sandwiches. After eating, Castiel checked his watch and saw that they still had another half hour before they needed to leave for the concert hall. He kissed Dean gently, enjoying the wax of the lipstick make their lips stay in contact. Pulling away for air, Dean blushed at seeing Cas with transferred lipstick on. He grabbed a paper towel and gently dabbed the rouge off of Castiel's naturally dark pink lips. Castiel looked at Dean fondly during the process.

Before Dean was able to set the paper towel back down, Cas was already leaning over to suckle his ear lobe. Dean gasped and shuddered from Castiel's heated voice, "I can't wait to blow you, Dean. Head under your skirt, sucking you down."

"Jesus fuck! Cas, stop being such a tease!" Dean whined while squeezing Castiel’s ass. The older man moaned loudly before reluctantly pulling away. They exchanged fond looks before Cas bussed the dishes and Dean went to the bathroom to fix up his lipstick. Castiel called out that he was going to wait outside with the tickets. Dean enjoyed the fact that his lover didn’t ever object riding shotgun in the Impala.

Dean walked out to the car as Castiel locked the front door. Just for kicks, Dean held open the passenger door for Cas. Castiel kissed his cheek before getting into the car. As Dean got into the driver’s seat, he was glad he didn’t go for those black 2.5 inch heels. The one inch ones alone were making his driving experience alien and dirty.

Castiel frowned at the 21 year old wondering what was wrong. Soon those cherry lips sighed and suddenly Cas had the Mary Janes on his lap. He blushed lightly trying to restrain his awe at his partner on his face. Dean finally turned on the engine and pulled out from the curb. They didn’t talk much but the silence was good. Dean got excited to find a free parking spot that could handle the Impala. Castiel hid his smile at the other’s enthusiasm.

Dean slipped the shoes back on before getting out of the car to see a large group of women mingling in front of the concert hall wearing similar outfits. They seemed oblivious of his gender and commented on how cute he looked. He blushed but was afraid to speak. Castiel walked over quickly after getting their tickets taken care of. “She’s pretty shy. Um, if you could excuse us.”

Dean felt incredibly awkward. The women gave him pitied looks that he caught in the corner of his eye as Castiel took him towards the band set-up. He sighed, “Dude, that was fucking horrible.”

“Come on, De. It wasn’t that bad. They were rather convinced. I think they were sad by how such a pretty woman could be so timid.”

“Ugh. No,” Dean exasperated with an eye roll. “I’m still pretty sure I’m 100% man.”

Castiel kissed his cheek, “You would give my old gender studies professor a conniption, you rare snow flake. Let’s get a drink.”

They walked over to the bar off to the side of the hall to get a rum and coke for Dean and a cosmo for Castiel.

“Goddamn, how can you drink that?” Dean stared at Castiel as the man sipped the alcoholed down cranberry juice. Castiel shrugged, “I prefer not to drink sugary junk.”

“Weirdo,” Dean grumbled. After a pause, he laughed. Castiel shook his head and found two seats by the bar for them. They watched the musicians set up and do their sound checks. The crooner for the night got up to the mic and started up a happy banter with the crowd of 200 so people. It was interesting how the music was still so popular even in 2000.

As the last musician gave their nod of readiness, the whole band started up the first song. The singer was encouraging the crowd to get up and dance the night away. Dance their worries away.

Castiel and Dean weren’t quite done with their drinks but once the first song came to an end, Castiel asked for Dean’s hand. This was one of the few aspects of their relationship where Castiel was the lead. Dean never learned how to dance until Castiel gave him lessons. Cas had been forced to take ballroom as a preteen since his old fashioned parents figured that would give him an edge in society. It really didn’t. But it felt wonderful to swing a breathless beauty like Dean around the dance floor. Cas even took a dance lesson during their first month of courtship to freshen up his rusty dance moves. Dean had only found out when the blabber mouth Balthazar told him about how a wonderful student Castiel was during a waltz party they were attending. Dean didn’t take offense to it, instead he encouraged Castiel to take more lessons. Balthazar was still trying to get Dean into his dance studio, but the young man refused.

As the first hour of boisterous music wore on, the hall became raucous with dancing bodies. The dancing was sensual and passionate without being vulgar. Dean loved feeling Castiel’s firm grip on his waist as they moved to the beat. Castiel would always get a silly smile on his face during any dance that was upbeat. When the music became more slow and fluid, the smile became more serious. It made Dean feel like he was the only thing that exists in Castiel’s world.

In a way, he was. Castiel had serious puppy love for the guy that grew into something more meaningful. Castiel was truly in love with Dean. He didn’t want to scare the guy with such intense feelings. They had been so light hearted and enjoying their time at concerts, the record shop that Dean worked at part time, and under the sheets. Castiel didn’t want to end it.

Dean would be lying if he hadn’t noticed Castiel’s jerky body language lately. It felt like the man was hiding something. Dean was a little worried that maybe the fake tits was the last nail in the coffin for this summer romance. Dean wanted more but was scared. This would be his first relationship. Well, technically they had been dating for almost three months. He never really thought about it until it hit him. He had been getting all of the attention he craved from just Castiel. He hadn’t thought of anyone else since that Queens of the Stone Age concert.

As the final song ended with the crooner asking if anyone wanted to party with the band afterwards. Dean looked at Cas curiously.

“Nah, there’s something better I want to do,” Castiel whispered into his ear. Dean blushed and felt his cock harden against the band of his underwear. They wandered out of the concert hall with the crowd of dancers still jabbering away on the last fumes of the night’s adrenaline. Once they were in the cool air of the starry night, Castiel tugged on Dean’s hand, “Come on, I want to go to the park.”

“Um, okay,” Dean tried to hide his panic but the blush of fear on his chest appeared. Castiel had seen it before when Dean’s brother caught them necking in the Impala after a punk rock concert. Castiel felt awful and rubbed Dean’s back with a soothing intent. Dean’s breathing still had a tremble but the blush was receding. Castiel sat down on the large tire swing and pulled Dean to sit on it facing him.

“So, I don’t want to scare you,” Castiel cursed himself the moment those words came out. They were the wrong ones. Dean’s mascara was slowly going down his cheeks. “I meant that I know you haven’t had a relationship before. And feelings are not really your favorite thing to talk about. I don’t want to scare you because I do love you. I mean, you’re really amazing, Dean. I can’t help but have deeper feelings for y-”

Dean forced Castiel to stop rambling by kissing hard. Dean had always been better at conveying feeling through action. And by the small moan from Castiel, Dean was glad the older man understood what Dean was getting at. Their kisses got more involved until Cas lost his balance on the swing and flailed about. Dean was cackling hard while trying to help out the man who loved him. The man who loved him. That was a hard punch in the gut but left a warmth instead of an ache. “I think I love you too, Cas.”

With only the night sky to illuminate Castiel’s face, his wide eyes behind his glasses and an open mouth caught between an exhale and an inhale were imprinted in Dean’s mind. “Thank you, Dean. I was afraid I was being one sided.”

Dean laughed, “Dude, really? This was never one sided. C’mon, let’s go to your place. It’s getting a little chilly.”

After disentangling themselves from the tire swing, they walked quickly to the Impala. Dean was humming a little of the piano solo they danced a mean foxtrot to. Castiel looked up to the sky to thank whoever who was looking back down. The ride back to the little yellow house was very quick since no one was out at 11 pm on a Thursday night.

Castiel unlocked the door and turned on the living room light before pulling Dean into a hard kiss. They became far more vocal with need than in the park. “D-Dee, can I?” Castiel slipped a hand under the skirt of the dress. His fingers ghosted up the firm thigh and his eyes widened to feel the panties Dean had been wearing that night. Dean usually stuck to briefs or tight boxers whenever he would cross dress. But Castiel was definitely feeling stretchy lace and a narrow band of cotton between.

Dean growled canting his hips up, “Suck me off, Cas.”

Castiel moaned and fell to his knees. With the extra height from the shoes, Cas was mouth level to the loosely confined bulge. Feeling a rush of taboo desire, he kept his gaze up at Dean as he lifted the skirt up to get under it. Dean cursed aloud. He felt the dress become tighter against the backs of his legs as the dark haired man settled between his legs. Dean felt soft breathy moans against his crotch before gentle fingers pulled the panties down his hips to his knees. A wet softness went up his cock causing his eyes to roll back in his head. It was better than being blindfolded. To only see the bobbing of Cas’ head under the pink skirt and feel all of the sensations that mouth was causing. Then a sharp squeeze of Dean’s ass jolted him back into himself to only shake and whimper as the filthy sounds of Cas’ humming throat taking Dean’s cock down deep filled his ears.

Castiel was loving the sensation of fucking his face on Dean’s cock. The rough denial of air made him light headed and the taste of precum was going to stay for hours. After a few intense moments of using his throat, he allowed his jaw to rest as he kissed his numb lips down the spit wet cock to Dean’s balls. Licking slowly, Cas enjoyed the whines and pleas from his lover. He gently sucked one into his mouth before greedily sucking the other one in as well. Feeling his jaw ache from the odd angle, he moved his tongue around before moving away for air. He licked his lips cutting off the trail of spit that had been connected to the twitch ballsack and his lower lip. He closed his eyes enjoying the pleas of his name that were semi muffled from the pink fabric. This was one of the reasons he was so supportive of Dean’s cross dressing. It enabled him to live out his little world of worshipping Dean’s cock in privacy from even Dean.

He knew Dean didn’t like to be penetrated but the guy loved to be “eaten out like a lesbian.” Cas pulled down the panties all the way to the floor and nipped a quaking inner thigh. He purred hearing the sharp cry from above. Then he removed his glasses and spread Dean’s ass enough to press the flat of his tongue against the light pink hole.

“Oh, fuck. Cas! Finger yourself as you lick me out, babe! Gotta fuck you after this,” Dean whined as his hips rolled into Cas’ mouth. His legs were on the verge of buckling and he was seeing stars float by. Strong hands held him up which was good, but it meant Cas wasn’t prepping himself. “Babe! Fucking make yourself ready! I can stand just fine as you eat me out.”

Castiel groaned as he pulled away to pull down his pants and briefs. He ripped open the lube sachet he had in his back pocket for in case they would do a quickie at the concert hall. The lube eased his fingers into his ass as he went back to tonguing Dean’s ass. The dirty talk was far more arousing to Castiel than the two fingers stretching him open.

“Good boy. Getting open for me to fill? Gonna fuck you into that couch, babe. Gonna make you scream. Maybe scream that you love me and my cock.”

The visuals sent Cas’ mind over the edge and he slipped away from the dress and quickly tried to get as naked as possible while Dean kicked the panties from his feet and held them up. “You want these in your mouth?”

Cas stared at him in awe. The thought of being gagged with panties of all things had never crossed Castiel’s mind before. But once he thought about it, his head was already nodding a yes. Dean pulled him into a kiss before biting down on his lip and growling, ”Open.”

Castiel dropped his jaw eagerly and felt the dry musky sensation of balled up panties in his mouth. He groaned while looking up into Dean’s eyes to see that most mascara had stained the beautiful man’s cheeks. Castiel couldn’t help but wipe away the kohl before bending over the back of his couch. Dean was quickly behind him and lined up his cock against Cas’ ass. “So hot seeing you like this, babe. Your ass is begging better than your slutty mouth.”

Castiel let out a long moan as Dean spat at his spasming hole before pushing his cock in. Dean held up his skirt between his teeth with a growl watching those pale shoulder blades roll before him with each thrust. At first, Dean thought Cas was playing up his enthusiasm to bottom, but no, this was 110% Castiel. “Stop, cockwhore,” Dean bit out with the fabric between his teeth.

Dean smirked as Castiel whined at the order but obeyed. The younger man then took his time with languid thrusts. He enjoyed the pressure from the spasming insides of the stock still man before him. Dean smirked and shifted his thrusts to hit Castiel’s prostate over and over. Dean wasn’t going to last much longer so he might as well try to get Castiel from 0 to 60 in a few seconds.

It did the trick. Castiel was wailing behind the panties and nearly tearing the black upholstery of his couch. He loved trying to push himself to his limits. Obeying Dean’s kinky orders was the hardest but most fulfilling experience for the 26 year old. Before he could comprehend it, he felt himself get jerked off in time of the punishing thrusts and spilling his seed. Dean grunted as he pulled out to flip Cas onto the couch face up. Castiel was breathing hard through his nose while looking drained yet eager to please. Dean came around to lean over his lover and kiss him hard over the gagged lips. There was a faint trace of lipstick left on each of their lips as Dean pulled away taking the ruined panties away with his own mouth. Tossing them to the floor, he took Cas’ hand and placed it on his cock. Castiel jerked him off to orgasm in less than a minute as they held eye contact.

“Love you.”

The phrase was murmured from both men at the same time. Dean blushed before heading into the bathroom to get a towel. Castiel had nodded off for a moment with a lazy smile once Dean came back into the living room. Dean wiped them both down before getting the sleepy man into his bed. There was a slight pause of Dean debating whether to join Cas or not. Thankfully Castiel made the decision by tugging on the dress for Dean to come closer. Dean yawned as he got naked and curled up to Castiel. The older man pulled him into his arms and that’s all he remembered before waking up from the morning sun and wake up hickies.

 

**Author's Note:**

> Follow me on [Tumblr](http://www.mesmeretmarjorie.tumblr.com) For updates and when I will be working on a new piece for the WMW! [ Watch Me Write](https://docs.google.com/forms/d/1G1Z_a9Rx2R3ixl5sKpO6bj8lLAnxSv5P6m0PvZEE7N8/viewform)


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